Green vat dyes and process of making them.



are ATNT FIUUE- MICHAEL KAIRDOS, OF CHARLOTTENI BURG, GERMANY, ASSIGNOR TO BADISCHE ANILIN (5c SODA FABRIK, OF LUDWIGSHAFEN-ON-THE-RHINE, GERMANY, A CORPORATION.

GREEN VAT DYES AND PROCESS OF MAKING THEM.

No Drawing.

To all whom it may concern:

Be it known that 1, MICHAEL KARnos, citizen of Hungary, residing at Charlottenburg, Germany, have invented new and use ful Improvements in Green Vat Dyes and Processes of Making Them, of which the following is a specification.

I have discovered new green vat coloring matters of the anthracene series which are characterized by being soluble in alkaline hydrosulfite solution giving red solu tions. I can obtain my new coloring matters by subjecting to the action of a molten caustic alkali a product obtainable by acting on aceanthrene quinone with hydroxylamin and which I regard as an oxim and hereinafter refer to under this name. Instead of employing aceanthrene quinone, I can make use of a halogen derivative thereof and for the purposes of this invention I regard such halogen derivatives as being equivalent to aceanthrene quinone. ther, the hydroxylamin can be replaced by an equivalent thereof, such as a body which gives rise to hydroxylamin. Instead of subjecting the compounds hereinbefore termed oXims to the action of an alkaline melt, T

can first treat them with acids, for instance with glacial acetic acid, in the presence of hydrochloric acid and acetic anhydrid, or with concentrated sulfuric acid, whereupon compounds are obtained which are probably imids of anthracene-1.9-dicarboxylic acid or halogen derivatives thereof. The said imids, on treatment with molten caustic alkali, also give rise to the new green vat coloring matters of this invention.

Aceanthrene quinone is described by.

Liebermann in Bem'chte vol. 44, page 204, and probably has a constitution corresponding to the formula ll regard aceanthrene quinone oxim as pos Specification of Letters Patent.

Fur-

Patented Feb. 13, 19117.

Application filed .Tune 30, 1913. Serial No. 776,541.

sessing the constitution corresponding to the formula OC--C=NOH UV'V and I, further, regard anthracene-1.9- d carboxylic acid lmld as possessing a constltutlon corresponding to the formula The following examples will serve to illustrate further the nature of my invention and how it can be carried into practical effect, but the invention is not confined to these examples. The parts are by weight.

Example 1.

Introduce, while stirring, 2 parts of the product obtainable from hydroxylamin and aceanthrene quinone, which is hereinbefore referred to as an oXim, into 12 parts of molten commercial caustic potash, while maintaining a. temperature of from 210 to 230 C. Continue heating the melt for about 10 minutes at this temperature and then pour it into water, while stirring. Add 25 parts of a 30% solution of acetic acid and pass air through the solution until the original red-violet color has disappeared and no more separation takes place. Then filter, wash the product until the filtrate is neutral and dry the residue which is soluble in alkaline hydrosulfite solution yielding a cherry red vat which colors cotton red-violet shades, which shades, on exposure to air, become beautiful full green.

A similar procedure can be followed in order to obtain vat coloring matters from alena the condensation products of halogenated I aceanthrene quinone and hydroxylamin.

V hereinbefore as anthracene 1.9 dicarboxylic acid imid with 5 parts of caustic alkali and a small quantity of water at from 200 to 230 C. until the formation of the 'color:

ing matter is complete. Allow the melt to cool, dissolve it in water, neutralize a part of the alkali and pass air through the solution, whereupon a green coloring matter is precipitated in flakes. If desired, the oxidation can be carried out by other means. The coloring matter is soluble in alkaline hy drosulfite solution yielding a cherry red vat which colors cottonred-violet shades which shades, on exposure to" the air, become a beautiful full green.

A similar procedure can be followed when employing a corresponding compound obtained from a halogenated aceanthrene quinone.

Now what I claim is:

1. The new vat coloring matters of the.

are soluble in alkaline hydrosulfite solution so giving red solutions and which (lye cotton beautiful full green shades of excellent fastness.

2. The new vat coloring matter of the anthracene series obtainable by melting anthracene-1.9-dicarboxylic acid imids with caustic alkali, which new coloring matter is soluble in alkaline hydrosulfite solution yielding a cherry red vat which colors cot ton red-violet shades, which shades, on ex- 4 posure to air, become a beautiful full green. 3. The process of producing vat coloring matters of the anthracene series by first treating an aceanthrene quinone oxim body with-an acid and-then subjecting the prod uct to the action of an alkaline melt. 4. In the process of producing vat color ing matters of the anthracene series, the

step which consists in subjecting anthracene-1.9-dicarboxylic acid action of a caustic alkaline melt.

In testimony whereof I have hereunto set my hand in the presence of two subscribing witnesses.

MICHAEL KARDOS. Witnesses:

' OTTO GLAUF,

ADALBERT Mosnovrrs.

imid. to the W i 

